A group of 1-thio-beta-L-fucopyranosides containing hexadecane, 9-octadecene, adamantane, 1,2-diphenyltetrafluoroethane, and 3-hexynyl- and 3,6-dioxaoctylcholesterols were synthesized as potential immunologic adjuvants. Many of these fucosyl lipids and 6-(5-cholesten-3 beta-yloxy)hexyl 1 thioglycosides were found to give good response to subunit A/Victoria influenza virus. Carbohydrates with L-fucose and D-galactose backbones appeared essential for adjuvant activity. Lactose which has a terminal D-galactose moiety was found to be active, whereas L-arabinose which lacks a 5-(hydroxymethyl) group was inactive.
New glycolipid compounds, process for preparation and use as immunological adjuvant
申请人:Merck & Co., Inc.
公开号:EP0023865A2
公开(公告)日:1981-02-11
Compounds of the formulae Y-R wherein Y is 1-thio-B-L-fucose, 1-thio-B-D-galactose or 1-thio-B-lactose and R is 2-(1- adamantyl) ethyt, 3- [(p-tetrafluorophenethyl) phenyl] propyl, 6-(5-cholesten-3B-yloxy) hex-3-ynl, oleyl, or hexadecyl are useful immunologic adjuvants in vaccines.
Y-R 式中 Y 为 1-硫代-B-L-岩藻糖、1-硫代-B-D-半乳糖或 1-硫代-B-乳糖,R 为 2-(1-金刚烷基)乙基、3-[(对氟苯乙基)苯基]丙基、6-(5-胆甾烯-3B-氧基)己-3-炔基、油基或十六烷基的化合物是疫苗中有用的免疫佐剂。
US4259324A
申请人:——
公开号:US4259324A
公开(公告)日:1981-03-31
Glycolipids as potential immunologic adjuvants
作者:Mitree M. Ponpipom、Robert L. Bugianesi、Tsung-Ying Shen
DOI:10.1021/jm00185a007
日期:1980.11
A group of 1-thio-beta-L-fucopyranosides containing hexadecane, 9-octadecene, adamantane, 1,2-diphenyltetrafluoroethane, and 3-hexynyl- and 3,6-dioxaoctylcholesterols were synthesized as potential immunologic adjuvants. Many of these fucosyl lipids and 6-(5-cholesten-3 beta-yloxy)hexyl 1 thioglycosides were found to give good response to subunit A/Victoria influenza virus. Carbohydrates with L-fucose and D-galactose backbones appeared essential for adjuvant activity. Lactose which has a terminal D-galactose moiety was found to be active, whereas L-arabinose which lacks a 5-(hydroxymethyl) group was inactive.